1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine

Chemical compound From Wikipedia, the free encyclopedia

1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine is a drug developed by a team led by Alan Kozikowski, which acts as a potent dopamine reuptake inhibitor, and was developed as a potential therapeutic agent for the treatment of cocaine addiction.[1] As with related compounds such as nocaine, it is a structurally simplified derivative of related phenyltropane compounds.[2] Its activity at the serotonin and noradrenaline transporters has not been published, though most related 4-phenylpiperidine derivatives are relatively selective for inhibiting dopamine reuptake over the other monoamine neurotransmitters. While several of its isomers are active, the (3S,4S)-enantiomer is by far the most potent.[3][4] The rearranged structural isomer 2-[1-(4-chlorophenyl)butyl]piperidine is also a potent inhibitor of dopamine reuptake.[5]

2-[1-(4-chlorophenyl)butyl]piperidine[6]
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Quick facts Identifiers, CAS Number ...
1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine
Identifiers
  • (3S,4S)-4-(4-Chloro-phenyl)-1-methyl-3-propyl-piperidine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC15H22ClN
Molar mass251.80 g·mol−1
3D model (JSmol)
  • CCC[C@@H]1CN(CC[C@@H]1C2=CC=C(C=C2)Cl)C
  • InChI=1S/C15H22ClN/c1-3-4-13-11-17(2)10-9-15(13)12-5-7-14(16)8-6-12/h5-8,13,15H,3-4,9-11H2,1-2H3/t13-,15-/m1/s1
  • Key:MWGRXFWGMDSMNI-UKRRQHHQSA-N
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